The Chicago skyline and Lake Michigan at departure offer a more visually striking and recognizable scene than the distant, hazy mountain silhouette near Madrid, even though both sides are otherwise similar given the long featureless ocean crossing in between.
Flown MDW to MAD? Did we get it right?
Flight Path
Chicago to Madrid is 4,190 miles (6,744 km), a flight of about 8 hours 20 minutes.
North Atlantic Ocean for several hours, with possible distant sighting of the southern Irish coast near Cork before the descent into continental Europe begins over northern Spain.
Great circle distance and headings ›Phase by phase

Takeoff from MDW
LEFTMidway sits just south of downtown Chicago, so climbing out on an eastbound departure puts the Loop skyline and Lake Michigan's shoreline on the left side of the aircraft. It's a brief but genuinely distinctive urban view before the flight turns toward open water and farmland.

Landing at MAD
RIGHTUnder Madrid's typical north-flow configuration, arrivals come in from the south and the final turn onto the runway can bring the Sierra de Guadarrama into view ahead and to the right, contrasting with the flat plains of La Mancha crossed just before. It's a modest but real terrain feature that the flatter southern approach lacks.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Barajas (MAD)?
Sit on the Left side of the plane for the best views on flights from Chicago to Madrid. The Chicago skyline and Lake Michigan at departure offer a more visually striking and recognizable scene than the distant, hazy mountain silhouette near Madrid, even though both sides are otherwise similar given the long featureless ocean crossing in between.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Left side for the best views. Midway sits just south of downtown Chicago, so climbing out on an eastbound departure puts the Loop skyline and Lake Michigan's shoreline on the left side of the aircraft. It's a brief but genuinely distinctive urban view before the flight turns toward open water and farmland. Notable sights include: Chicago Loop skyline, Lake Michigan shoreline, Willis Tower, Navy Pier area.
What can I see when landing at Barajas in Madrid?
When landing at Barajas (MAD), sit on the Right side for the best views. Under Madrid's typical north-flow configuration, arrivals come in from the south and the final turn onto the runway can bring the Sierra de Guadarrama into view ahead and to the right, contrasting with the flat plains of La Mancha crossed just before. It's a modest but real terrain feature that the flatter southern approach lacks. Notable sights include: Sierra de Guadarrama foothills, Jarama river valley, Madrid's northern suburbs, Barajas terminal complex.
How long is the flight from Chicago to Madrid?
The flight from Chicago Midway International (MDW) to Barajas (MAD) takes about 8 hours 20 minutes. The shortest flight path between them is 4,190 miles (6,744 km); winds and air traffic control usually add a few percent.
What does the Chicago to Madrid flight path pass over?
North Atlantic Ocean for several hours, with possible distant sighting of the southern Irish coast near Cork before the descent into continental Europe begins over northern Spain.